Android and Apple mobile devices have taken the market by storm.  Not only are they being used by consumers but they are now being used for critical functions in businesses, hospitals, government and more.   This trend is expected to continue with the popularity of mobile devices such as tablets well into the future.  In this presentation we put Android up against Apple iOS to determine which, if any, are ready for enterprise or federal use.  Once and for all we battle the Apple App Store vs. Google Play, device updates, developer controls, security features and the current slew of vulnerabilities for both devices.  Which platform will emerge the victor?  You might find that while the "tech is hot" the implementation and built in security controls are "not". 

1. Android vs. Apple iOS Security Showdown
Tom Eston

2. About Your Presenter
• Tom Eston CISSP, GWAPT
• Manger of the SecureState Profiling & Penetration Team
• Specializing in Attack & Penetration, Mobile Security
• Founder of SocialMediaSecurity.com
• Facebook Privacy & Security Guide
• Security Blogger – SpyLogic.net
• Co-host of Social Media Security Podcast
• National Presenter
Black Hat USA, DEFCON, ShmooCon, SANS, OWASP
2

3. Agenda
• The Latest Statistics on Android vs. Apple iOS
• Android and Apple iOS Overview – Versions & Features
• What are the issues, what are the security concerns?
• The “SHOWDOWN”!
– Each feature compared between Android and Apple
iOS…who will win??
• Mobile Device Best Practices
3

4. Android?
4

5. Apple?
5

6. It’s a SHOWDOWN!
Image: PinoyTutorial.com 6

7. Android - Latest Statistics
• 300 Million Devices Sold
(as of February 2012)
• 450,000 apps in the Android Market (Google Play)
7

8. Apple iOS - Latest Statistics
• 316 Million iOS Devices Sold (as of February 2012)
• Increase due to Verizon/Sprint now selling Apple
devices
• 500,000 apps in the Apple App Store
8

9. 9

10. What Do We See?
• Apple iOS is the most talked about, more widely
deployed
– iPad’s are hot!
• Android a close second
• BlackBerry third
• Windows Mobile fourth
• webOS or Symbian OS?
10

11. Android: Current Versions
• Jelly Bean 4.1.1
– Tablet (Nexus 7) and Nexus Phone
• Honeycomb 3.2.6
– Tablet only (Motorola Xoom)
• Updates are periodic. No set schedule by Google.
• Updates to the device depend on the hardware
manufacturer and the cell carrier
• Samsung Galaxy Nexus and the Nexus 7 tablet get
updates immediately from Google (this is the ‘Google
Phone/Tablet’)
11

12. Apple iOS: Current Versions
• Not to be confused with Cisco “IOS”
• Apple changed the name to “iOS” in
June 2010
• Updated at least once a quarter, mostly
minor revisions
• Current version(s):
– All carriers (GSM/CDMA) = 5.1.1
– iOS 6 in Beta 2
• iOS 5 fully supports iPhone 4/4S, iPhone
3GS, iPod Touch 3/4 gen, iPad 1-3
12

13. Mobile Security Concerns
• App Store and Mobile Malware
• App Sandboxing
• Remote Wipe and Policy Enforcement
• Device and App Encryption
• OS Updates
• Jailbreaking and Rooting
• New(er) Technology
13

14. App Stores and Mobile Malware
• Android Marketplace (now Google Play)
– Very little application vetting, previous issues with
Malware in the Marketplace (working on
improving this)
– Hot target for malware and malicious apps
– Easy to get users to install popular “fake” apps
outside Google Play
14

15. Recent Mobile Malware Statistics
• Juniper Networks’ 2011 Mobile Malware Threats Report
– 13,302 samples of malware found targeting Android
from June to December 2011
– “0” samples of malware found targeting Apple iOS
(seriously…)
Source: http://www.juniper.net/us/en/local/pdf/additional-
resources/jnpr-2011-mobile-threats-report.pdf
15

16. Legend of Zelda on Android?
This would be awesome if true! ☺
http://nakedsecurity.sophos.com/20
12/04/26/dirty-tricks-android-apps/
16

17. Angry Birds from Unofficial App Stores
• Disguised as a Trojan horse
• Uses the “GingerBreak”
exploit to root the device
• Your device becomes part
of a botnet
http://nakedsecurity.sophos.com/2012/04/12/a
ndroid-malware-angry-birds-space-game/
17

18. Easy to Ignore Android App
Permissions
• Reminder: Some apps
can do things you
didn’t know about
– Example:
Launching the web
browser
18

19. Example: Fake Instagram App
19

20. App Stores and Mobile Malware
• Apple App Store
– Developers must pay $99
– Submit identifying documents
(SSN or articles of incorporation for a company)
• Google Play
– Developers must pay $25
– Agree to a “Developers Distribution Agreement”
– Easy to upload lots of apps and resign if apps get
rejected or banned
20

21. App Stores and Mobile Malware
• Apple App Store
– Vetting process for each app in the store
– Must pass Apple’s “checks” (static analysis of binaries)
– Code for each app is digitally signed by Apple, not
the developer
• Process was exploited by Charlie Miller in November of
2011
– Created an “approved” app which was digitally signed
– The app later downloaded unsigned code which could
modify the OS dynamically
– Was a bug in iOS 4.3/5.0
21

22. Apple’s Problem? Questionable Apps
• 90% of submissions to the Apple App Store are denied
because the app doesn’t do what it says it does
• Spammy apps…mainly privacy issues such as UDID usage
• Jailbroken device? More susceptible to malware from
unauthorized app repositories (Cydia)
• Apps that look like legitimate apps:
– Temple Run -> Temple Guns -> Temple Jump
– Angry Birds -> Angry Ninja Birds -> Angry Zombie Birds
– Zombie Highway -> Zombie Air Highway
22

23. Angry Zombie Birds is Real!
23

24. …and it’s horrible!
FAIL! 24

25. Apple: Very Little App
Permissions Shown To Users
• Mainly for privacy
• Apps are limited to what
they can do
• * Apps can access contact
data without permission
(will be fixed in iOS 6)
• Developers can do this on
their own (Yelp)…
25

26. 26

27. Recent Apple “Find and Call Malware”
• First “Trojan” for Apple
iOS?
• Really it was a spammy
app that sent your
contact list to a third-
party server
• Your friends get SMS
spammed from the
server
• Contact list notification
to be added in iOS 6
• App removed from the
App Store and Google
Play
Image: Kaspersky Labs 27

28. Winner: Apple iOS
• Apple’s “walled garden” works better than Android’s
“open garden” (at least for now)
• However, still not immune from spammy, fake or
potentially malicious apps (or really bad games)!
28

29. Android: App Sandboxing
• Privileged-Separated Operating System
– Each app runs with a distinct system identity
• Unique Linux user ID and group ID for each app
• No app, by default, has permissions to perform
operations that would impact other apps, the OS,
or the user (Android Developer Docs)
– The app grants permissions outside the default
“sandbox”
• Location based services can only be disabled
globally, not on a per app basis
– Apps are “signed” by the developer (not Google) and
can be self-signed certificates (not a security feature)
29

30. Android: App Sandboxing
– Google “community based” enforcement
• If the app is malicious or not working correctly
the App community will correct the problem
(in theory)
– Rooted device? Too bad…root can access the
keystore!
• Apps can write to the SD Card (removable storage)
– Files written to external storage are globally
readable and writable
30

31. Apple iOS: App Sandboxing
• Each app is installed in
its own container
• If the app is
compromised via
exploit, the attacker is
limited to that container
• Jailbroken device?
Ignore the last bullet
point…
Image: iOS Developer Library (developer.apple.com)
31

32. Apple iOS: App Sandboxing
• Each app is signed by Apple (not the developer)
• Apps run as the “mobile” user
• The Keychain is provided by Apple outside the sandbox
for password or sensitive data storage
• Apps can only access Keychain content for the
application
– Also a “device protection” API can be used by
developers
– Note: There are tools to dump the Keychain but the
device has to be Jailbroken (in some form)
• Apple does not use external storage devices (SD Cards)
32

33. Winner: Apple iOS (by a nose)
• Apple signs all applications
• Limited areas to store app data
• Permissions system is simpler for
users
– Example: More granular
control of location based
settings
• Keychain and device protection
APIs help
(if developers use them)
33

34. Remote Wipe and Policy Enforcement
• Android
– Google Apps Device Policy ($$)
– Third-Party App ($$)
– Third-Party MDM (Mobile Device Management) ($$)
– Microsoft Exchange ActiveSynch
• Apple iOS
– Google Apps Device Policy ($$)
– Apple OS X Lion Server Profile Manager ($$)
– FindMyPhone (Free)
– iPhone Configuration Utility (Free)
– Third-Party MDM ($$)
– Microsoft Exchange ActiveSynch
34

35. Android: Remote Wipe
• Google Apps Device Policy (Full MDM)
– Need a Google Apps Business Account
– Can manage multiple devices
• iOS, Windows Mobile and Android
35

36. 36

37. Apple iOS: FindMyPhone
• Free and easy way to remote
wipe or find a lost or stolen
device
• Accessible via icloud.com
37

38. Android: Policy Enforcement
• Android Device Administration API
– Encrypt data stored locally
– Require password
– Password strength
– Minimum characters
– Password expiration
– Block previous passwords
– Device auto lock
– Device auto wipe after failed password attempts
– Allow camera (not supported on Android, only iOS)
– Encrypt device (whole disk)
– Remote wipe/lock
38

39. Android Policy Enforcement
• No free utility to provision or
create profiles
• Need to create an app to
install specific settings
• Android provides little
guidance on how to deploy
this app
• Users must activate the app
for policies to take effect
39

40. Apple iOS: Policy Enforcement
• Very detailed settings available:
– Passcode
– Wi-Fi
– VPN
– Proxy
– LDAP
– Exchange ActiveSynch
– App/Camera and other Restrictions
– …and more!
40

41. iPhone Configuration Utility
41

42. Winner: Apple iOS
• Free remote wipe utility (FindMyPhone)
• Much more granular enterprise controls
• Free small scale MDM (iPhone Configuration Utility)
• Easier to implement policies
42

43. Device and App Encryption
• Android
– No device encryption on Android < 3.0
– Device encryption API released in “Ice Cream
Sandwich – 4.0”
– Based on dm-crypt (disk encryption)
– API available since 3.0 for app level encryption
43

44. Device and App Encryption
• Apple iOS Hardware Encryption
– Hardware encryption was introduced with the iPhone
3GS
– Secures all data “at rest”
– Hardware encryption is meant to allow remote wipe
by removing the encryption key for the device
– Once the hardware key is removed, the device is
useless
– Full MDM API’s available
44

45. Device and App Encryption
• Apple iOS Device Protection
– “Device Protection” different than “Hardware
Encryption”
– This is Apple’s attempt at layered security
• Adds another encryption layer by encrypting
application data
• Key is based off of the user’s Passcode.
– Only Mail.app currently supports this
– Many developers are not using the APIs
– Often confused with Hardware Encryption
45

46. Winner: Apple iOS
• Slight edge to Apple for having hardware based
encryption
• Device Protection API more robust than Android
• Developer documentation +1 for Apple
46

47. OS Updates
• Android
– Slow patching, if at all!
– OTA updates
– A lot depends on forces outside of Google
– Some devices will not support the latest version
of Android…ever!
– Google releases the update or patch, device
maker customizes it, then carrier customizes it as
well…
47

48. 48

49. Android Device Fragmentation
*3,997 distinct devices downloaded OpenSignalMaps app in 6 months:
http://opensignalmaps.com/reports/fragmentation.php? 49

50. OS Updates
• Apple iOS
– Frequent updates (at least once a quarter)
– Easier for Apple because the hardware is the
same, not device manufacturer or carrier
dependent
– iOS 5 brings OTA updates
50

51. Winner: Apple iOS
• Same hardware, updates from one source = easier
and faster to update
• Track record of (more) quickly addressing security
issues
51

52. Jailbreaking and Rooting
“Jailbreaking essentially reduces iOS security to the
level of Android…”
– Dino Dai Zovi, iOS Hacker
52

53. Rooting on Android
• Allows “root” access (super user) to the device
• Why do people “root”?
– Access the flash memory chip (modify or install a
custom ROM)
– Make apps run faster
– Remove device or carrier apps
– Turn the phone into a WiFi hotspot to avoid carrier fees
– Allows “Unlocking” so the device can be used with
another cell provider
• Rooting is LEGAL in the United States
– Digital Millennium Copyright Act (DMCA 2010)
53

54. Rooting Process on Android
54

55. Jailbreaking on Apple iOS
• Full access to the OS and file system
• Install applications and themes not approved by
Apple (via installers like Cydia)
• Tether their iOS device to bypass carrier restrictions
• They hate Apple’s communist and elitist restrictions
• Jailbreaking is LEGAL in the United States
– Digital Millennium Copyright Act (DMCA 2010)
55

56. Jailbreaking Tools
• Pwnage Tool
• Redsn0w
• Sn0wbreeze
• GreenPois0n Absinthe
• Jailbreakme.com
• LimeRa1n exploit used
for most Jailbreaks
56

57. New Jailbreaks
• Latest versions of Absinthe and redsn0w can
Jailbreak all new Apple devices running 5.1.1 (4S and
the “new” iPad)
• iOS 6 beta already jailbroken (tethered only)
• iPhone dev-team does fantastic work!
57

58. Winner? None!
• Rooting and jailbreaking are bad for the security of the
device!
• Malware for Android takes advantage of this…and in
some cases roots the device for you
• Previous iOS “worm’s” that look for SSH ports from
jailbroken devices
• Removes built in sandbox restrictions
• MDM needs to prevent and/or detect rooted and
jailbroken devices!
(you should also have a policy)
58

59. New(er) Mobile Technology
• Both devices are coming out with more innovative
features which have interesting security considerations
• Android 4.0 has facial recognition to unlock the device
– Potential issue with the “swipe pattern” feature vs.
standard passcode unlock
• ASLR (Address Space Layout Randomization)
– New in Android 4.0
– Support since iOS 4.3
– Developers have to take advantage of this!
– * Kernel ASLR added in iOS 6
59

60. New(er) Mobile Technology
• Android: NFC
– Android Beam
– Let’s see how
NFC gets
attacked at
Black Hat USA
this year…
60

61. New(er) Mobile Technology
• Android: NFC
– Google Wallet
61

62. New(er) Mobile Technology
• Apple iPhone 4S –
Siri Voice Control
• Allows commands
by default on a
locked device
• Send emails/text’s
and more…
Image: Sophos
62

63. Mobile Device Best Practices
(for Android or Apple iOS)
☺
63

64. The Passcode
• You should always have a passcode
• You should require it immediately
• It should be > 4 characters, 6 is recommended
6 character Alphanumeric = 196 years to brute force!
– Why so long? You have to do the attack on the
device…
• It should be complex
• Enable lockout/wipe feature after 10 attempts

65. Enable Remote Management
• For true Enterprise level management you must use
a third-party MDM
– Decide which type of enrollment is best for you
– Whitelist approach may be best
• Allow only devices you have authorized
• BYOD: policy sign-off?

66. Don’t Allow Rooting or Jailbreaking
• Removes some built-in security features and
sandboxing
• Can leave you vulnerable to malicious applications
• Ensure third-party MDM solutions prevent or detect
rooting/jailbreaking
• Address this in your mobile device policy

67. Android Specific Best Practices
• Enable Password Lock Screen vs.
Face Unlock or Pattern
• Disable USB Debugging
• Enable Full Disk Encryption
• Download apps only from official
app stores
– Google Play
– Amazon
67

68. Where to Find More Information
• Links to all the tools and articles mentioned in this
presentation:
http://MobileDeviceSecurity.info
• My presentations:
http://SpyLogic.net

69. Thank you for your time!
Email: teston@securestate.com
Twitter: agent0x0
QUESTIONS
ANSWERS
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